The Power of Trying: Why You Must Take Leaps Into Unknown Te…

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In 1894, a New York Times writer warned against the dangers of riding a bicycle, predicting that it would lead to “weakness of mind, general lunacy and homicidal mania.” In 1925, the dean of Princeton University asserted that cars would make young people “look lightly at the moral code.” For years, I’ve kept a collection of these bonkers predictions. They’ve always struck me as funny — and, critically, as proof that innovation isn’t as scary as it seems. I think about them anytime someone confuses “new” with “threatening.” And then one day, it hit me: This would make a great podcast.

Did I know how to podcast? Not a clue. But it seemed like a fun idea. A friend gave me a used microphone, I teamed up with a guy I met on Twitter and I googled for what software to use. Then I spent three months making the first episode of a show called Pessimists Archive. When it came out, I thought, Hooray! I’m a podcaster! And then I realized I hadn’t even begun making a second episode. That took another two months. It’s been a year now, going on and on like this, often laboring at night after my son goes to bed.

I haven’t made a dime on it. But I’ve kept at it. It’s still exciting. And more important, I’ve learned that a project like this — in which I hone a new skill, even with no foreseeable payoff — can have benefits in the most unexpected of ways. I learned how to produce a podcast on the fly and how to build a small team around a passion project. (Four of us now work on the show.) I also learned how to build an audience from scratch, which I never had to do working for magazines. Best of all, as I continually tweak how we make the show, I’ve gotten into the habit of questioning how and why I do everything.

And after a year, the experience paid off in a more direct way, too. My Entrepreneur colleagues recently began talking about building a podcast network. Thanks to my past experience, I was able to help guide the conversation. Then I developed the first show we launched. It’s called Problem Solvers, a weekly series about entrepreneurs solving unexpected problems in their businesses. I love how open entrepreneurs are about their challenges, and I wanted to create a show that captures that honesty and ingenuity. When we learn how smart people think, we all get smarter. (Forgive the quick sales pitch: Search for Problem Solvers on iTunes or wherever you get your podcasts. I think you’ll like it!)

But the biggest takeaway from my little experiment is that we have to take leaps. Some people think only in terms of ROI; they want to know that time invested will lead to a direct payout. I get it. But the fact is, we can never know exactly how, when or why something we do will pay off. Our careers and businesses aren’t straight lines; they aren’t predictable or perfectly controllable. They’re simply a series of opportunities — and when a great one comes along, we need to be able to say, “Sure, let’s give it a shot.”

That’s why I think we all should keep jumping into projects like this, even if we don’t know how (or if) they’ll pay off. Entrepreneurs need to play a long game. The future is unknowable, full of challenges and potential. But we do know this: The more wisely we spend our time today — the more we take risks, and search for new passions and figure out new things as we go, stumbling around in the dark until we’re better and smarter and more skilled than we were before — the more versatile and capable and satisfied we’ll be tomorrow.

Come to think of it, maybe that’s the subject for another good podcast.